N⁴,N^4'-dibenzyl-N⁴,N^4'-dimethyl-[1,1'-biphenyl]-4,4'-diamine | 1254951-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N⁴,N^4'-dibenzyl-N⁴,N^4'-dimethyl-[1,1'-biphenyl]-4,4'-diamine
• 英文别名: N-benzyl-4-[4-[benzyl(methyl)amino]phenyl]-N-methylaniline
• CAS: 1254951-71-7
• 化学式: C₂₈H₂₈N₂
• 分子量: 392.544
• InChiKey: JNYJCEONBPQCIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-甲基苄基苯胺 在 iron(III) chloride hexahydrate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以77%的产率得到N⁴,N^4'-dibenzyl-N⁴,N^4'-dimethyl-[1,1'-biphenyl]-4,4'-diamine
  参考文献：
  名称：

  FeCl 3 ·6H 2 O促进苯胺的氧化偶合反应合成联苯胺衍生物

  摘要：

  在烧瓶条件下，在可商购的FeCl 3 ·6H 2 O的存在下，N，N-二取代苯胺可以转化为功能多样的联苯胺，收率最高为99％。氧化偶联作用扩展至N-单取代苯胺，并将该方法用于有效制备6,6'-联喹啉。还进行了机械研究以解释观察到的反应性。

  DOI：

  10.1021/jo4002504

文献信息

• Synthesis of Benzidine Derivatives via FeCl₃·6H₂O-Promoted Oxidative Coupling of Anilines
  作者：Xuege Ling、Yan Xiong、Ruofeng Huang、Xiaohui Zhang、Shuting Zhang、Changguo Chen

  DOI：10.1021/jo4002504

  日期：2013.6.7

  Under open-flask conditions in the presence of commercially available FeCl3·6H2O, N,N-disubstituted anilines can be converted into diversely functionalized benzidines with yields of up to 99%. Oxidative coupling was extended to N-monosubstituted anilines, and the method was applied to the efficient preparation of 6,6′-biquinoline. Mechanistic investigations have also been performed to explain the observed

  在烧瓶条件下，在可商购的FeCl 3 ·6H 2 O的存在下，N，N-二取代苯胺可以转化为功能多样的联苯胺，收率最高为99％。氧化偶联作用扩展至N-单取代苯胺，并将该方法用于有效制备6,6'-联喹啉。还进行了机械研究以解释观察到的反应性。
• Oxidative Coupling of<i>N</i>,<i>N</i>-Dialkylanilines Using Iodic Acid and Sodium Nitrite
  作者：Sameerana N. Huddar、Ulhas S. Mahajan、Krishnacharya G. Akamanchi

  DOI：10.1246/cl.2010.808

  日期：2010.8.5

  A new reagent system, a combination of iodic acid and sodium nitrite has been investigated for oxidative coupling of N,N-disubstituted anilines. A facile para-selective coupling occurs to give benz...

  研究了一种新的试剂系统，即碘酸和亚硝酸钠的组合，用于 N,N-二取代苯胺的氧化偶联。一种简单的对选择性耦合发生使苯...
• Extension studies on iron(III)-promoted free radical oxidation of anilines: self-coupling and self-bridged assembling reactions
  作者：Jing Pan、Jiaqiang Li、Ruofeng Huang、Xiaohui Zhang、Hang Shen、Yan Xiong、Xiangming Zhu

  DOI：10.1016/j.tet.2015.06.018

  日期：2015.8

  The iron(III)-promoted free radical oxidation of anilines has been further developed. Anilines including those bearing strong electron-withdrawing groups on benzene ring were readily converted into corresponding self-coupling benzidines. With addition of base, the methyl on nitrogen was activated and the free radical oxidations tended to furnish the corresponding self-bridged assembling diaminodiarylmethanes. (C) 2015 Elsevier Ltd. All rights reserved.
• Electrochemical synthesis of symmetrical benzidines through dehydrogenative cross-coupling reaction
  作者：Xiaoying Liu、Tian-Cheng Cai、Dingyi Guo、Bin-Bin Wang、Shengneng Ying、Huixian Wang、Shiyun Tang、Qinpeng Shen、Qing-Wen Gui

  DOI：10.1016/j.tetlet.2021.153021

  日期：2021.4

  Synthesis of diversely functionalized symmetrical benzidines through electrochemical dehydrogenative cross-coupling reaction of two N,N-disubstituted anilines, is described. The reactions conducted under mild conditions with no oxidizing reagents and transition metal catalysts.

  描述了通过两个 N，N-二取代苯胺的电化学脱氢交叉偶联反应合成多种功能化的对称联苯胺。反应在温和条件下进行，无需氧化试剂和过渡金属催化剂。